US5376675A - Control of parasitic nematodes (A) - Google Patents
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- US5376675A US5376675A US08/070,391 US7039193A US5376675A US 5376675 A US5376675 A US 5376675A US 7039193 A US7039193 A US 7039193A US 5376675 A US5376675 A US 5376675A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Definitions
- This invention relates to the control of diseases caused by parasitic nematodes in plants and mammals.
- the present invention provides the use of the compound 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) ##STR2## or an acid addition salt thereof, for use in controlling diseases caused by parasitic nematodes in plants, including crops, and in mammals.
- DMDP 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine
- the invention also includes seeds, dressed, coated or impregnated with DMDP or a said salt thereof.
- the mechanism through which DMDP controls diseases caused by parasitic nematodes in plants may include any nematotoxic, nematostatic or anti-feedant effect on either adult or juvenile nematodes, inhibition of hatching of larval forms of nematodes, inhibition of root gall formation by nematode feeding, and further extends to any effect on a nematode that prevents its acquisition and/or transmission of plant viruses.
- DMDP is of natural origin and has been shown to display low phytotoxicity.
- a further advantage of DMDP lies in its mode of application when treating plants, especially crops.
- Many existing anti-nematode compounds are applied to the soil by broadcasting and incorporated using rotary cultivation.
- DMDP can be applied to the leaves, which, somehow produces an anti-nematode action in the roots of the plant. Possibly DMDP is translocated through the phloem, but this is not certain.
- DMDP may be applied in the form of a foliar spray instead of or in addition to the above-mentioned conventional means of application.
- a suitable dosage for soil application of DMDP is from at least 24 to at most 48 kg/ha at 20 cm depth.
- DMDP may also be applied by pre-treating plant seeds before sowing.
- DMDP is water-soluble and can therefore be applied without a surfactant or dispersing agent.
- concentration of active ingredient and rate of application depend on the mode of application and type of effect desired, e.g. they may differ for nematotoxicity and for inhibition of virus transmission.
- foliar spraying it is suggested that normally the plants be sprayed with a solution containing 0.01 to 3-5 g./liter, preferably 0.01 to 1.0 g./liter of the active ingredient, until the spray runs off. Lower concentrations can be more useful in some circumstances, while higher concentrations will often be tolerable.
- DMDP displays its properties against a wide range of nematodes affecting plants, e.g. root-knot nematodes, cyst nematodes and virus-transmitting nematodes.
- root-knot nematodes e.g. root-knot nematodes
- cyst nematodes e.g. cyst nematodes
- virus-transmitting nematodes e.g. root-knot nematodes, cyst nematodes and virus-transmitting nematodes.
- crop-damaging nematodes of the following genera: Meloidogyne, Globodera, Heterodera, Radopholus, Pratylenchus, Hirschmanniella, Scutellonema, Helicotylenchus, Tylenchus, Rotylenchus, Ditylenchus, Longidorus, Xiphinema.
- DMDP is active against a wide range of helminthic nematodes, especially those of the following genera: Haemonchus, Teladorsagia, Nematodirus, Trichostrongylus, Dictyocaulus and Cooperia, particularly the species Haemonchus contortus and Teladorsagia circumcincta (previously classified as Ostertagia circumcincta).
- DMDP may be extracted from Derris elliptica Benth (Leguminosae) as described by A. Welter et al (Phytochem., 1976, 15, 747-749) or may be synthesized from D-glucose (Fuhrman et al., Nature, 1984, 307, 755-758); G. W. J. Fleet and R. W. Smith Tetrahedron Letters 26 (11) 1465-1468 (1985) or from L-sorbose (P. Card et al., J. Org. Chem., 1985, 50, 891-893).
- DHDP applies also to its acid addition salts, which can be any which are compatible with the intended use, e.g. agriculturally or veterinarily acceptable if the use is on plants or non-human animals respectively.
- Such salts can be made in the conventional way from the free base.
- the effect of a chemical on virus acquisition by a nematode vector was tested by exposing virus-free nematodes to a virus infected source plant in the presence of the test chemical. By comparing subsequent rates of virus transmission between treated and untreated nematodes the efficacy of the chemical can be determined.
- Whether a chemical affects the transmission of the virus can be determined by applying the chemical after the nematodes have acquired the virus, at the time they are about to feed on receptor plants.
- Petunia seedlings were potted in 22 ml of 3:1 sand/loam mixture. Forty-eight hours later the plants were inoculated with virus. After a further 24 hours 5 adult nematodes were added to each pot. (The test chemicals are added at this time if virus acquisition is being tested.) There were 10-15 replicates of each treatment. After 4 weeks the nematodes were extracted, and then added to the soil in which virus-free receptor plants were growing. (If virus transmission is being tested, the test chemicals are added at this time.) After a further 4 weeks the nematodes were again extracted and counted. The galls on the roots of the receptor plants were counted, the roots macerated and the sap applied to the leaves of Chenopodium quinoa plants (virus indicators).
- the chemicals tested were DMDP (15 and 30 ppm) and a conventional nematotoxic compound oxamyl (7 ppm).
- Table 1a shows the effect of DMDP inhibiting root gall formation and per cent virus acquisition as compared to the control value.
- Table 1b shows the effect of DMDP inhibiting root gall formation and per cent virus transmission as compared to the control value.
- the hatch test examines the effect of the test chemicals on the egg hatch of Globodera pallida, the white Potato Cyst Nematode (PCN).
- PCN Potato Cyst Nematode
- Table 2a shows the number of hatched juveniles, dead or alive, as the means from four replicates. The same data are also expressed as % effect. This Table shows that DMDP greatly decreases the number of juveniles hatching from cysts.
- Table 2b shows the % decrease in nematodes alive as compared to the control after 4 weeks. From Table 2b, it can be seen that DMDP provides better effects than its acid salt.
- Table 3a shows the in vitro toxicity of DMDP over a range of concentrations. The percent immobility shown is corrected for control immobilities using Abbott's formula. Note the decrease in in vitro toxicity at 200 ppm and above. There is also an anomalous drop in toxicity at 25 ppm.
- Table 3b shows the EC 50 values (effective concentration required to immobilise 50% of the total number of nematodes) calculated from the results.
- Table 4 shows the dose-dependent activity of DMDP, using three tests: the split-pot experiment, the mini-pot experiment and the gall test experiment.
- the test shows whether the anti-nematode agents of the invention have a repellent or antifeedant effect on the nematodes and/or a nematicidal effect.
- a ⁇ split-pot ⁇ i.e. a pot divided into two sections by a fine mesh material (see Alphey et al, Revue Nematol. 1988, 11(4), 399-404), was used. Each side was filled with 37 ml of soil (3:1 sand:loam mixture). Test compounds at the concentrations shown in Table 4 were added to the soil on the side in which a Petunia seedling had been planted. To the other side 100 adult Xiphinema diversicaudatum were added. There were 8 replicates of each treatment.
- Table 4a(i) shows that DMDP has an antifeedant action against nematodes at all concentrations tested.
- Table 4a(ii) shows that 80 ppm DMDP also possesses a nematotoxic effect in that on the plant side more nematodes were immobilised than in the pot to which oxamyl was applied.
- Petunia seedlings were planted in 22 ml of soil (sand:loam--3:1).
- the test compound solution or water (control) with 5 or 10 adult Xiphinema diversicaudatum were added to the soil. There were 10 replicates for each treatment. After 3 weeks the nematodes were extracted and the number of galls induced by nematode feeding on the roots were recorded and expressed as a mean per cent reduction of the control value.
- Table 4b shows that DMDP has a nematode repellent or antifeedant action.
- the most effective rate of DMDP was 25 ppm.
- Table 4c shows the results, from which it will be seen that DMDP is equally effective in the range 2.5-25 ppm but less effective at 50 and 240 ppm. The various tests indicate similar levels of activity of DMDP used between 2.5 ppm and 100 ppm
- the mini-pot test was adapted.
- the roots of Petunia hybrida were removed and the cut ends of the stems from which the newly formed roots were growing were put in a solution of test compound (concentration as shown in Table 5) for 24 hours prior to the start of the experiment.
- the effects of these treated plants to X. diversicaudatum were compared to that of plants whose cut ends had been immersed in water for 24 hours.
- Table 5 shows that root uptake following soil application is a suitable method of treatment with DMDP.
- test compounds were administered by being painted on to the leaves of the tomato seedlings.
- DMDP was tested on three different plant species at 200 ppm for 14 days using methods outlined in the mini-pot test. The seedlings were then left to grow for 16 days and the % growth measured relative to control plants. Root length and shoot length were also measured.
- Small 60 ml clear canisters were filled with approximately 25 g soil. 1 ml test compound and 1 ml water containing 1500 PCN eggs was added. Small pieces of Desiree potato with sprout were placed into the compost. Lids pierced 3-4 times were used to close the canisters. The canisters were then put on a tray, covered with black polythene and Kept at a constant 20° C. After 4 weeks the first cyst count was taken, then every following week until the end of the eighth. Table 7 shows the % reduction in cysts, as compared to the control. It can be seen that DMDP was effective in reducing the number of cysts developing.
- Example 5 As an extension to Example 5, further experimentation was undertaken in sand and soil, or a variety of plants and nematodes to demonstrate the different methods of applying DMDP.
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Abstract
The use of the compound 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) ##STR1## or an acid addition salt thereof in controlling diseases caused by parasitic nematodes in plants or mammals.
Description
This invention relates to the control of diseases caused by parasitic nematodes in plants and mammals.
Since the early 1940s many chemical compounds active against plant parasitic nematodes have been available. These have often displayed undesirable toxic effects, for example the fumigant dibromochloropropane was withdrawn from the market in 1977, as it was thought to cause sterility in workers. During the 1960's fumigant type nematicides were largely superseded by granular systemic nematicides. These have been in use since then, a representative compound being oxamyl. These compounds are mainly oximecarbamates or organophosphate derivatives, and because of their toxicity have to be used in a strictly controlled manner. Accordingly it would be of benefit to have anti-nematode agents that are environmentally favourable, i.e. being non-toxic themselves and in their degradation products to non-target organisms.
Additional prior art is referred to in a separate section after "Summary of the Invention", without which its context would not be clear.
The present invention provides the use of the compound 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) ##STR2## or an acid addition salt thereof, for use in controlling diseases caused by parasitic nematodes in plants, including crops, and in mammals. The invention also includes seeds, dressed, coated or impregnated with DMDP or a said salt thereof.
The mechanism through which DMDP controls diseases caused by parasitic nematodes in plants may include any nematotoxic, nematostatic or anti-feedant effect on either adult or juvenile nematodes, inhibition of hatching of larval forms of nematodes, inhibition of root gall formation by nematode feeding, and further extends to any effect on a nematode that prevents its acquisition and/or transmission of plant viruses.
DMDP is of natural origin and has been shown to display low phytotoxicity.
The discovery and extraction of DMDP is described by L. E. Fellows and G. W. J. Fleet in "Alkaloid Glycosidase Inhibitors from Plants" (In "Natural Products Isolation", G. H. Wagman and R. Cooper, Eds., Elsevier, Amsterdam, 1988, pp 540-565). In that review certain properties of DMDP, including insecticidal and insect deterrent activity, both as determined experimentally in feeding tests, are referred to. They are more clearly described in L. E. Fellows, Chemistry in Britain pp 842-844 (1987). These and other properties of DMDP are more extensively reviewed in Chapter 11 of "Plant Nitrogen Metabolism", Plenum Publishing Corporation, 1989, pp 395-427, by L. E. Fellows et al., especially at pages 410 (which refers to S. V. Evans et al., Entomol. Exp. Appl. 37, 257-261 (1985), 411 (which refers to the authors' own work and to W. M. Blaney et al., Entomol. Exp. Appl. 36, 209-216 (1984) and 415. See also L. E. Fellows et al., in "Swainsonine and Related Glycosidase Inhibitors", L. James, A. D. Elbein, R. J. Molyneux and C. D. Warren, Eds., Iowa State University Press, 1989, pp 396-416. The properties of DMDP referred to therein are not indicative of an anti-nematode effect.
A further advantage of DMDP lies in its mode of application when treating plants, especially crops. Many existing anti-nematode compounds are applied to the soil by broadcasting and incorporated using rotary cultivation. DMDP can be applied to the leaves, which, somehow produces an anti-nematode action in the roots of the plant. Possibly DMDP is translocated through the phloem, but this is not certain. Hence, DMDP may be applied in the form of a foliar spray instead of or in addition to the above-mentioned conventional means of application. A suitable dosage for soil application of DMDP is from at least 24 to at most 48 kg/ha at 20 cm depth. DMDP may also be applied by pre-treating plant seeds before sowing.
DMDP is water-soluble and can therefore be applied without a surfactant or dispersing agent. The preferred concentration of active ingredient and rate of application depend on the mode of application and type of effect desired, e.g. they may differ for nematotoxicity and for inhibition of virus transmission. For foliar spraying it is suggested that normally the plants be sprayed with a solution containing 0.01 to 3-5 g./liter, preferably 0.01 to 1.0 g./liter of the active ingredient, until the spray runs off. Lower concentrations can be more useful in some circumstances, while higher concentrations will often be tolerable.
DMDP displays its properties against a wide range of nematodes affecting plants, e.g. root-knot nematodes, cyst nematodes and virus-transmitting nematodes. Of particular note is its activity against the crop-damaging nematodes of the following genera: Meloidogyne, Globodera, Heterodera, Radopholus, Pratylenchus, Hirschmanniella, Scutellonema, Helicotylenchus, Tylenchus, Rotylenchus, Ditylenchus, Longidorus, Xiphinema. With regard to nematodes which infest mammals, DMDP is active against a wide range of helminthic nematodes, especially those of the following genera: Haemonchus, Teladorsagia, Nematodirus, Trichostrongylus, Dictyocaulus and Cooperia, particularly the species Haemonchus contortus and Teladorsagia circumcincta (previously classified as Ostertagia circumcincta).
DMDP may be extracted from Derris elliptica Benth (Leguminosae) as described by A. Welter et al (Phytochem., 1976, 15, 747-749) or may be synthesized from D-glucose (Fuhrman et al., Nature, 1984, 307, 755-758); G. W. J. Fleet and R. W. Smith Tetrahedron Letters 26 (11) 1465-1468 (1985) or from L-sorbose (P. Card et al., J. Org. Chem., 1985, 50, 891-893).
The above description of DHDP applies also to its acid addition salts, which can be any which are compatible with the intended use, e.g. agriculturally or veterinarily acceptable if the use is on plants or non-human animals respectively. Such salts can be made in the conventional way from the free base.
The following Examples illustrate the invention. "Tween" is a Registered Trade Mark. The units "ppm" signify a solution containing mg. of test compound per liter of water, in solutions for in vitro tests or in solutions for application to leaf surfaces. In the Examples, "DMDP" means the free base.
The effect of a chemical on virus acquisition by a nematode vector was tested by exposing virus-free nematodes to a virus infected source plant in the presence of the test chemical. By comparing subsequent rates of virus transmission between treated and untreated nematodes the efficacy of the chemical can be determined.
Whether a chemical affects the transmission of the virus can be determined by applying the chemical after the nematodes have acquired the virus, at the time they are about to feed on receptor plants.
Experiments were performed in 25 cm3 plastic pots maintained in temperature controlled cabinets (Taylor & Brown, Nematol. medit., 1974, 2, 171-175) using three week old seedlings of Petunia hybrida Vilm. The nematode/virus combination used was Xiphinema diversicaudatum vectoring Arabis Mosaic Virus.
Petunia seedlings were potted in 22 ml of 3:1 sand/loam mixture. Forty-eight hours later the plants were inoculated with virus. After a further 24 hours 5 adult nematodes were added to each pot. (The test chemicals are added at this time if virus acquisition is being tested.) There were 10-15 replicates of each treatment. After 4 weeks the nematodes were extracted, and then added to the soil in which virus-free receptor plants were growing. (If virus transmission is being tested, the test chemicals are added at this time.) After a further 4 weeks the nematodes were again extracted and counted. The galls on the roots of the receptor plants were counted, the roots macerated and the sap applied to the leaves of Chenopodium quinoa plants (virus indicators).
Twelve days later the C. quinoa plants were examined for the symptoms of the virus. There were 10-15 replicates of each treatment in both virus tests. In all cases controls were run in which no chemicals were added.
The chemicals tested were DMDP (15 and 30 ppm) and a conventional nematotoxic compound oxamyl (7 ppm).
Table 1a shows the effect of DMDP inhibiting root gall formation and per cent virus acquisition as compared to the control value.
Table 1b shows the effect of DMDP inhibiting root gall formation and per cent virus transmission as compared to the control value.
TABLE 1a
______________________________________
Feeding and acquisition of Arabis Mosaic Virus
by Xiphinema diversicaudatum
Mean No. % virus No. of
Treatment galls/root acquisition
Replicates
______________________________________
Control 1.5 33 15
DMDP 15 ppm 0.5 (66%) 27 (18%) 15
DMDP 30 ppm 0.4 (74%) 7 (79%) 14
Oxamyl 7 ppm
0.3 (80%) 0 (100%) 10
______________________________________
() is % reduction in treatment compared to control
TABLE 1b
______________________________________
Feeding and transmission of Arabis Mosaic Virus
by Xiphinema diversicaudatum
Mean No. % virus No. of
Treatment galls/root transmission
replicates
______________________________________
Control 1.5 64 11
DMDP 15 ppm
0.4 (74%) 72 (0%)* 10
DMDP 30 ppm
0.5 (66%) 18 (72%) 11
Oxamyl 7 ppm
0.7 (53%) 1 (98%) 11
______________________________________
() is % reduction in treatment compared to control
*treatment values higher than control
The hatch test examines the effect of the test chemicals on the egg hatch of Globodera pallida, the white Potato Cyst Nematode (PCN).
Ten PCN cysts of uniform size and colour were put in a tube with 0.25 ml of the test compound solution (concs. 50 ppm and 100 ppm) and 0.75 ml of potato root diffusate. Root diffusate normally stimulates the juveniles to hatch from eggs in the cysts. There were 4 replicates of each treatment. Twice each week the liquid was removed and the number of hatched live and dead juveniles counted. The diffusate/chemical mixture was replenished after each nematode count. The tubes were stored at 19° C. between counts.
Table 2a shows the number of hatched juveniles, dead or alive, as the means from four replicates. The same data are also expressed as % effect. This Table shows that DMDP greatly decreases the number of juveniles hatching from cysts.
This experiment was repeated using Globodera rostochiensis. Table 2b shows the % decrease in nematodes alive as compared to the control after 4 weeks. From Table 2b, it can be seen that DMDP provides better effects than its acid salt.
TABLE 2a
______________________________________
Potato Cyst Nematode Hatch Test
Hatched Juveniles
Total Juveniles
Live Dead Hatched
Treatments (% increase)*
(% increase)*
(% decrease)*
______________________________________
15 days exposure
Control 698 16 714
DMDP 50 ppm
374 (46) 68 (325) 442 (38)
DMDP 100 ppm
203 (71) 91 (468) 294 (59)
24 days exposure
Control 1257 32 1289
DMDP 50 ppm
1056 (16) 112 (250) 1168 (9)
DMDP 100 ppm
601 (52) 150 (368) 751 (42)
______________________________________
TABLE 2b
______________________________________
Globodera rostochiensis cyst Hatch Test
Conc (ppm)
Test Compound
220 100 50 25 12.5 6.25 3.12
______________________________________
DMDP 32 38 52 52 41 0 10
DMDP.HCl 0 0 0 0 27 31 21
______________________________________
*All percentages are based on the control value
Groups of ten active adult Xiphinema diversicaudatum were hand-picked into individual watchglasses containing distilled water. At a given time the batches of nematodes were transferred into 1 ml aliquots of test compound, at various concentrations of the test compound, or for the control into 1 ml of distilled water. There were three replicates of each treatment. At two intervals, viz. 48 and to 72 hours, the number of nematodes which were immobilised were recorded. They were considered as immobile if they failed to move when stimulated by prodding with a bristle. All tests were carried out at 5° C.
Table 3a shows the in vitro toxicity of DMDP over a range of concentrations. The percent immobility shown is corrected for control immobilities using Abbott's formula. Note the decrease in in vitro toxicity at 200 ppm and above. There is also an anomalous drop in toxicity at 25 ppm.
In similar tests differences in toxicity to adult and juvenile nematodes were found. Table 3b shows the EC50 values (effective concentration required to immobilise 50% of the total number of nematodes) calculated from the results.
This experiment was repeated, replacing X. diversicaudatum with Globodera rostochiensis. These results are shown in Table 3c, from which it can be seen that both DMDP and its acid salt are toxic to nematodes.
TABLE 3a
______________________________________
In vitro toxicity (adult Xiphinema diversicaudatum)
Conc (ppm)
10 25 50 100 200 500
Test compound
Percent immobility
______________________________________
DMDP 48 hrs 15 5 11 35 0 0
72 hrs 39 9 63 78 4 0
______________________________________
TABLE 3b
______________________________________
In vitro toxicity EC.sub.50 values (ppm) (Xiphinema diversicaudatum)
Nematode stage
Test duration
Test compound
tested 48 hrs 72 hrs
______________________________________
DMDP Adult 87.0 44.0
DMDP Juvenile 94.0 0.08
______________________________________
TABLE 3c
______________________________________
In vitro toxicity (Globodera rostochiensis)
Conc (ppm)
Test Compound
2.5 10 25 50 100
______________________________________
DMDP 25 37 44 50 37
DMDP.HCI 88 56 50 50 50
______________________________________
Table 4 shows the dose-dependent activity of DMDP, using three tests: the split-pot experiment, the mini-pot experiment and the gall test experiment.
a. Split-pot test
The test shows whether the anti-nematode agents of the invention have a repellent or antifeedant effect on the nematodes and/or a nematicidal effect.
A `split-pot`, i.e. a pot divided into two sections by a fine mesh material (see Alphey et al, Revue Nematol. 1988, 11(4), 399-404), was used. Each side was filled with 37 ml of soil (3:1 sand:loam mixture). Test compounds at the concentrations shown in Table 4 were added to the soil on the side in which a Petunia seedling had been planted. To the other side 100 adult Xiphinema diversicaudatum were added. There were 8 replicates of each treatment.
After 21 days the two halves of the pot were separated and the nematodes were extracted from the soil in each half. Root galls were recorded on plants from the treated sides (Table 4a(i)). The numbers of live and dead nematodes from each half were counted and are shown in Table 4a(ii).
Table 4a(i) shows that DMDP has an antifeedant action against nematodes at all concentrations tested. Table 4a(ii) shows that 80 ppm DMDP also possesses a nematotoxic effect in that on the plant side more nematodes were immobilised than in the pot to which oxamyl was applied.
b. Mini-pot test
This test identifies the nematicidal effect of the chemical in soil and its effect on nematode feeding behaviour.
Petunia seedlings were planted in 22 ml of soil (sand:loam--3:1). The test compound solution or water (control) with 5 or 10 adult Xiphinema diversicaudatum were added to the soil. There were 10 replicates for each treatment. After 3 weeks the nematodes were extracted and the number of galls induced by nematode feeding on the roots were recorded and expressed as a mean per cent reduction of the control value.
Table 4b shows that DMDP has a nematode repellent or antifeedant action. The most effective rate of DMDP was 25 ppm.
c. Gall test
In the gall test, tomato seedlings, stimulated to produce fine adventitious roots by removing the main root system, were planted in tubes containing 25 g of fine, sieved dry sand, 350 Meloidogyne incognita (J2) and DMDP, in solution in water. The effect of DMDP on the ability of the nematodes to gall the plant roots was studied over a 10-12 day period. A water control was included in the test. There were 10 replicates of each treatment.
Table 4c shows the results, from which it will be seen that DMDP is equally effective in the range 2.5-25 ppm but less effective at 50 and 240 ppm. The various tests indicate similar levels of activity of DMDP used between 2.5 ppm and 100 ppm
TABLE 4
______________________________________
4a.(i) Split-pot Experiment (X. diversicaudatum/Petunia)
Mean reduction galls/root
Chemical/conc (ppm)
as % of control
______________________________________
DMDP/15 63
DMDP/30 83
DMDP/80 89
______________________________________
______________________________________
4a.(ii) Mean numbers of nematodes recovered after 21 days in the
planted and non-planted sides of the split pot
(X. diversicaudatum/Petunia)
Total Mobile Immobile
Nematodes
Nematodes Nematodes
Test conc No No No
Chemical
(ppm) Plant plant
Plant plant
Plant plant
______________________________________
DMDP 16 27 15 24 10 3 5
DMDP 32 24 14 21 11 3 3
DMDP 80 25 15 12 11 13 4
Oxamyl 15 17 21 13 14 4 7
Control -- 33 16 31 12 2 4
______________________________________
______________________________________
4b. Mini-pot Experiment (X. diversicaudatum/Petunia)
Mean reduction
galls/root as % of control
Chemical/conc (ppm)
5 nematodes/pot
10 nematodes/pot
______________________________________
DMDP/8 70 --
DMDP/14 70 --
DMDP/25 94 72
DMDP/50 72 83
DMDP/100 65 100
______________________________________
______________________________________
4c. Gall Test (M. incognita/Tomato)
Chemical/conc (ppm)
Reduction in galls/root as % of control
______________________________________
DMDP/2.5 76
DMDP/12.5 70
DMDP/25 72
DMDP/50 50
DMDP/240 47
______________________________________
a) root application
To test whether the anti-nematode agent would be more effective when taken up systemically by plants, the mini-pot test was adapted. The roots of Petunia hybrida were removed and the cut ends of the stems from which the newly formed roots were growing were put in a solution of test compound (concentration as shown in Table 5) for 24 hours prior to the start of the experiment. The effects of these treated plants to X. diversicaudatum were compared to that of plants whose cut ends had been immersed in water for 24 hours. Table 5 shows that root uptake following soil application is a suitable method of treatment with DMDP.
b) foliar application
The mini-pot test and gall test described in Example 4 were repeated but the test compounds were administered by being painted on to the leaves of the tomato seedlings. In these tests, 0.4 ml test compound in solution in water at 200 ppm, or water alone, together with 0.05% "Tween 80" wetting solution, were painted onto the leaves.
The reductions in galling of 86% in the mini-pot test and 79% in the gall test, over the controls, show that the effect of the test compounds was expressed in the root system to provide protection against nematodes.
TABLE 5
______________________________________
Activity following uptake through root - details as in text
Mini-pot test: Petunia/Xiphinema diversicaudatum (21 days)
% reduction in root galling
Chemical/conc (ppm)
relative to controls
______________________________________
Oxamyl/50 92
DMDP/15 83
DMDP/30 100
DMDP/100 58
______________________________________
DMDP was tested on three different plant species at 200 ppm for 14 days using methods outlined in the mini-pot test. The seedlings were then left to grow for 16 days and the % growth measured relative to control plants. Root length and shoot length were also measured.
Table 6 shows the effect of DMDP on plant growth. All figures are % growth relative to controls (100%=same as control, >100%=greater than control).
Rye grass when treated with DMDP only grew to 65% of the control weight. This may not be significant in the field as the concentration of DMDP (200 ppm) used was twice its effective dosage required to control nematodes.
TABLE 6
__________________________________________________________________________
Phytotoxicity data (all at 200 ppm soil water)
Root length Shoot length
Total weight
Chemical
TOM OSR
RG TOM OSR
RG TOM OSR
RG
__________________________________________________________________________
Oxamyl
107 84 108 91 95 93 103 104
107
DMDP 90 98 105 90 97 74 100 100
65
__________________________________________________________________________
Plants
TOM = Tomato (cv. Moneymaker)
OSR = Oilseed rape (cv. Bienvenue)
RG = Rye grass (cv. Melle)
Small 60 ml clear canisters were filled with approximately 25 g soil. 1 ml test compound and 1 ml water containing 1500 PCN eggs was added. Small pieces of Desiree potato with sprout were placed into the compost. Lids pierced 3-4 times were used to close the canisters. The canisters were then put on a tray, covered with black polythene and Kept at a constant 20° C. After 4 weeks the first cyst count was taken, then every following week until the end of the eighth. Table 7 shows the % reduction in cysts, as compared to the control. It can be seen that DMDP was effective in reducing the number of cysts developing.
TABLE 7
______________________________________
Canister test (Globodera rostochiensis)
% reduction in cysts
Conc (ppm)
Test Compound
3.12 6.26 12.5 25 50 100 200
______________________________________
DMDP 7 0 14 46 43 35 7
DMDP.HCl 0 0 0 7 7 43 0
______________________________________
As an extension to Example 5, further experimentation was undertaken in sand and soil, or a variety of plants and nematodes to demonstrate the different methods of applying DMDP.
8(1) Sand Drench Test in a Tube
Glass tubes (7.5 cm×2.5 cm) were filled with 24.5 g sieved dried sand. 4 ml nanopure water was added and a hole made in the sand. 1 ml test compound and 1 ml water containing 350 Meloidogyne javanica were added immediately before a tomato seedling was planted in the hole. All tubes were then left for 14 days. In this experiment and in B(2) below, seedlings were prepared by having their roots cut off and fine adventitious roots allowed to regenerate prior to use. Table 8(1) shows the effect of DMDP and its acid salt over a range of concentrations. Results are shown as % reduction in live nematodes as compared to a control (no test compound).
8(2) Sand Foliar Test in a Tube
3 glass tubes (7.5 cm×2.5 cm) were filled with 24.5 g sieved dried sand. 5 ml nanopure water was added and a tomato seedling planted in the tube. Non-absorbant cotton wool was inserted around the base of the seedling to protect the sand from the test chemical to be sprayed. The tubes were placed in an incubator overnight. Next day, each plant was sprayed with 0.1 ml test chemical from an airbrush and returned to the incubator. On the following day, 1 ml water containing 350 Meloidogyne javanica was added to each tube. All tubes were then left for 14 days. Table 8(2) shows the effect of DMDP and its acid salt on a range of plants. Results are shown in % as in Table 8(1).
8(3) Foliar Application
2.5 cm pots were filled with 75 g of Levington universal and sand in a 3:1 ratio. Tomato plants (34 days old) were planted in these pots and 1 ml of water added. The soil was protected with filter paper and the pots left overnight in a glasshouse. Next day, each plant was sprayed with 0.3 ml test compound from an airbrush and then left in the glasshouse Overnight. Next day the filter paper was removed and 350 Meloidogyne javanica or Meloidogyne incognita in 1 ml water were added to the soil. The pots were then left for 12 days after which the number of live and dead nematodes were counted. Table 8(3) shows the effect of DMDP on a) Meloidogyne javanica and b) Meloidogyne incognita.
8(4) Soil Application
The procedure of 8(3) was repeated, except that on the first day, 1 ml test compound and 1 ml water with nematodes were added to the soil and the pots left for 14 days. Results are shown in the usual manner in Table 8(4).
TABLE 8(1)
______________________________________
Sand Drench
% reduction in galling by M. javanica
Conc (ppm)
Test Compound
200 100 50 25 10 5 1
______________________________________
DMDP.HCl 47 51 30 18 43 13
DMDP (Expt. 1)
77 72 79 76
DMDP (Expt. 2)
56 57 53 56 68 63 71
______________________________________
TABLE 8(2)
______________________________________
Sand Foliar
% reduction in galling by M. javanica
Conc (ppm)
Plant Test Compound
3200 2400 1600 800 400
______________________________________
Tomato DMDP 59 0 9
DMDP.HCl 18 5 9
Peppers DMDP 7 7 30 0
DMDP.HCl 9 0 7 0
Aubergines
DMDP 38 43 34 9
DMDP.HCl 44 50 19 19
______________________________________
TABLE 8(3)
__________________________________________________________________________
Soil Foliar % reduction in galling by a) M. javanica
b) M. incognita
Conc
Test Compound
1600
1000
800
400 200
100 50
25 10
1 0.1
__________________________________________________________________________
a) DMDP 27 27 22 22
a) DMDP 35 28 22 39
34
b) DMDP 24 24 26
30 31
b) DMDP 23
22
__________________________________________________________________________
TABLE 8(4)
______________________________________
Soil Drench % reduction in galling by a) M. javanica
b) M. incognita
Conc (ppm)
Test Compound
100 50 20 10 1.0 0.1 0.01
______________________________________
DMDP 28 19 21
DMDP 28 30 29 20 8
______________________________________
Claims (3)
1. A method of controlling diseases caused by nematodes in plants, which method comprises contacting said nematodes with a nematicidally effective amount of 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (DMDP) of formula: ##STR3## or an acid addition salt thereof in the vicinity of viable plant material.
2. A method according to claim 1, wherein DMDP is applied to the soil.
3. A method according to claim 1, wherein DMDP is sprayed onto the leaves of said plant.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9026271 | 1990-12-03 | ||
| GB909026271A GB9026271D0 (en) | 1990-12-03 | 1990-12-03 | Control of parasitic nematodes(a) |
| PCT/GB1991/002111 WO1992009202A1 (en) | 1990-12-03 | 1991-11-28 | Control of parasitic nematodes (a) |
Publications (1)
| Publication Number | Publication Date |
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| US5376675A true US5376675A (en) | 1994-12-27 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/070,391 Expired - Fee Related US5376675A (en) | 1990-12-03 | 1991-11-28 | Control of parasitic nematodes (A) |
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| US (1) | US5376675A (en) |
| EP (1) | EP0561820B1 (en) |
| JP (1) | JP2888978B2 (en) |
| CN (1) | CN1049557C (en) |
| AT (1) | ATE135527T1 (en) |
| AU (1) | AU658379B2 (en) |
| BR (1) | BR9107112A (en) |
| CA (1) | CA2097497C (en) |
| CY (2) | CY1883A (en) |
| DE (1) | DE69118204T2 (en) |
| ES (1) | ES2086554T3 (en) |
| GB (2) | GB9026271D0 (en) |
| HU (1) | HU213526B (en) |
| IE (1) | IE66397B1 (en) |
| IL (1) | IL100225A (en) |
| MX (1) | MX9102347A (en) |
| NZ (1) | NZ240826A (en) |
| PT (1) | PT99669B (en) |
| RU (1) | RU2091023C1 (en) |
| TR (1) | TR27540A (en) |
| WO (1) | WO1992009202A1 (en) |
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| ZW (1) | ZW17591A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962467A (en) * | 1995-06-07 | 1999-10-05 | Glycodesign, Inc. | Derivatives of swainsonine and their use as therapeutic agents |
| US6048870A (en) * | 1996-10-01 | 2000-04-11 | Glycodesign | 3, 5, and/or 6 substituted analogues of swainsonine processes for their preparation and their use as therapeutic agents |
| US6051711A (en) * | 1997-10-24 | 2000-04-18 | Glycodesign Inc. | Synthesis of swainsonine salts |
| US6395745B1 (en) | 1997-04-15 | 2002-05-28 | Glycodesign, Inc. | Alkaloid halide salts of swainsonine and methods of use |
| AU776245B2 (en) * | 1999-12-23 | 2004-09-02 | Prostalund Operations Ab | Method and device for the treatment of prostate tissue |
| US20060041599A1 (en) * | 1993-01-20 | 2006-02-23 | Masahi Tsuchida | Database management system and method for query process for the same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP4075977B1 (en) * | 2019-12-20 | 2024-02-07 | Universiteit Gent | Use of dehydroascorbic acid against nematode infection in plants |
| CN114369051B (en) * | 2022-01-06 | 2023-05-05 | 青岛农业大学 | Pyrrolidinol compound and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61118360A (en) * | 1984-11-13 | 1986-06-05 | Mitsubishi Chem Ind Ltd | Pyrrolidine derivative or its salt |
| EP0322395A1 (en) * | 1987-12-21 | 1989-06-28 | Monsanto Company | Heterocyclic compounds for inhibiting virus |
-
1990
- 1990-12-03 GB GB909026271A patent/GB9026271D0/en active Pending
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1991
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- 1991-11-28 WO PCT/GB1991/002111 patent/WO1992009202A1/en not_active Ceased
- 1991-11-28 EP EP91920397A patent/EP0561820B1/en not_active Expired - Lifetime
- 1991-11-28 ES ES91920397T patent/ES2086554T3/en not_active Expired - Lifetime
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- 1991-11-28 CA CA002097497A patent/CA2097497C/en not_active Expired - Fee Related
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- 1991-11-28 RU RU9193043997A patent/RU2091023C1/en not_active IP Right Cessation
- 1991-11-29 ZA ZA919447A patent/ZA919447B/en unknown
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- 1991-12-02 IE IE417691A patent/IE66397B1/en not_active IP Right Cessation
- 1991-12-02 IL IL10022591A patent/IL100225A/en not_active IP Right Cessation
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- 1991-12-03 CN CN91111920A patent/CN1049557C/en not_active Expired - Fee Related
-
1996
- 1996-04-05 CY CY188396A patent/CY1883A/en unknown
-
1998
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61118360A (en) * | 1984-11-13 | 1986-06-05 | Mitsubishi Chem Ind Ltd | Pyrrolidine derivative or its salt |
| EP0322395A1 (en) * | 1987-12-21 | 1989-06-28 | Monsanto Company | Heterocyclic compounds for inhibiting virus |
Non-Patent Citations (24)
| Title |
|---|
| Blaney et al, Entomol. exp. Appl, vol. 36, (1984) pp. 209 216. * |
| Blaney et al, Entomol. exp. Appl, vol. 36, (1984) pp. 209-216. |
| D. H. Janzen et al., "What Protects Lonchocarpus (Leguminosae) Seeds in a Costa Rican Dry Forest!", Biotropica 22 (3) 272-285 (1990). |
| D. H. Janzen et al., What Protects Lonchocarpus (Leguminosae) Seeds in a Costa Rican Dry Forest , Biotropica 22 (3) 272 285 (1990). * |
| Evans et al, Entomol. exp. Appl. vol. 37, (1985) pp. 257 261. * |
| Evans et al, Entomol. exp. Appl. vol. 37, (1985) pp. 257-261. |
| L. E. Fellows & G. W. J. Fleet, "Alkaloidal Gylcosidase Inhibitors from Plants" in Natural Products Isolation, ed. G. H. Wagman and R. Cooper, Elsevier Amsterdam (1988) pp. 540-565. |
| L. E. Fellows & G. W. J. Fleet, Alkaloidal Gylcosidase Inhibitors from Plants in Natural Products Isolation, ed. G. H. Wagman and R. Cooper, Elsevier Amsterdam (1988) pp. 540 565. * |
| L. E. Fellows et al., "Castanospermine, Swainsonine and related polyhydroxy alkaloids: structure, distribution and biological activity", in Plant Nitrogen Metabolism, ed. Jonathan E. Poulton, John T. Romeo and Eric E. Conn, Plenum Publishing Corporation (1989), pp. 395-427. |
| L. E. Fellows et al., "Polyhydroxy Plant Alkaloids as Glycosidase Inhibitors and their possible ecological role", American Chemical Society Symposium Series 296, Publication of symposium held Apr.-May 1985, Miami Beach, Chapter 6, pp. 72-76. |
| L. E. Fellows et al., Castanospermine, Swainsonine and related polyhydroxy alkaloids: structure, distribution and biological activity , in Plant Nitrogen Metabolism, ed. Jonathan E. Poulton, John T. Romeo and Eric E. Conn, Plenum Publishing Corporation (1989), pp. 395 427. * |
| L. E. Fellows et al., Polyhydroxy Plant Alkaloids as Glycosidase Inhibitors and their possible ecological role , American Chemical Society Symposium Series 296, Publication of symposium held Apr. May 1985, Miami Beach, Chapter 6, pp. 72 76. * |
| L. E. Fellows, "The Biological Activity of Parlyhydroxyalkaloids from Plants", pesticide Science 17, 602-606 (1986). |
| L. E. Fellows, The Biological Activity of Parlyhydroxyalkaloids from Plants , pesticide Science 17, 602 606 (1986). * |
| L. Fellows, "Botany breaks into the candy store", New Scientist, 45-48 (26 Aug. 1989). |
| L. Fellows, "Sugar-shaped bullets from plants", Chemistry in Britain, 842-844 (Sep. 1987). |
| L. Fellows, "The sugar-shaped weapons of plants", New Scientist, 40 & 41, 15 Aug. 1985. |
| L. Fellows, Botany breaks into the candy store , New Scientist, 45 48 (26 Aug. 1989). * |
| L. Fellows, Sugar shaped bullets from plants , Chemistry in Britain, 842 844 (Sep. 1987). * |
| L. Fellows, The sugar shaped weapons of plants , New Scientist, 40 & 41, 15 Aug. 1985. * |
| M. S. J. Simmonds et al. "Wild Plants a Source of Novel Anti-insect Compounds: Alkaloidal Glycosidase Inhibitors", in New Crops for Food and Industry, ed. G. E. Wickens, N. Haq and P. Day, (1989), Chapter 36, pp. 365-378. |
| M. S. J. Simmonds et al. Wild Plants a Source of Novel Anti insect Compounds: Alkaloidal Glycosidase Inhibitors , in New Crops for Food and Industry, ed. G. E. Wickens, N. Haq and P. Day, (1989), Chapter 36, pp. 365 378. * |
| M. S. J. Simmonds et al., "Behavioral and Electrophysiological Study of Antifeedant Mechanisms associated with Polyhdyroxy Alkaloids," J. Chemical Ecology 16 (11), 3167-3196 (1990). |
| M. S. J. Simmonds et al., Behavioral and Electrophysiological Study of Antifeedant Mechanisms associated with Polyhdyroxy Alkaloids, J. Chemical Ecology 16 (11), 3167 3196 (1990). * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060041599A1 (en) * | 1993-01-20 | 2006-02-23 | Masahi Tsuchida | Database management system and method for query process for the same |
| US5962467A (en) * | 1995-06-07 | 1999-10-05 | Glycodesign, Inc. | Derivatives of swainsonine and their use as therapeutic agents |
| US6048870A (en) * | 1996-10-01 | 2000-04-11 | Glycodesign | 3, 5, and/or 6 substituted analogues of swainsonine processes for their preparation and their use as therapeutic agents |
| US6395745B1 (en) | 1997-04-15 | 2002-05-28 | Glycodesign, Inc. | Alkaloid halide salts of swainsonine and methods of use |
| US6051711A (en) * | 1997-10-24 | 2000-04-18 | Glycodesign Inc. | Synthesis of swainsonine salts |
| AU776245B2 (en) * | 1999-12-23 | 2004-09-02 | Prostalund Operations Ab | Method and device for the treatment of prostate tissue |
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